Meet ​Paul Shaffer, David Letterman’s Longtime Bandleader and My Pseudo-Uncle

Paul Shaffer is best known as David Letterman's longtime bandleader and sidekick on Late Show with David Letterman. Shaffer has been with Letterman since the beginning, starting with the show's first incarnation, the riskier, arguably funnier Late Night with David Letterman, which aired on NBC from 1982 through 1993, and continuing through CBS's Late Show with David Letterman, which ends its 22-year run tonight. Combined, the shows have garnered 16 Emmy Awards and 112 Emmy Award nominations. During this time, Shaffer has been not just one, but two aces up Letterman's sleeve, able to liven up the stage with both music and comedy. He's got an impeccable sense of timing, and riffing—whether it's on a joke or on the piano—is his forte.

I didn't meet Paul in person until I was a teenager around 1998, at a Rock and Roll Hall of Fame ceremony back when they were held at the Waldorf Astoria in New York City. But, growing up, I always felt like I knew him. I had a habit of snooping through my pop's correspondence, and Paul was one of his buddies. Occasionally I'd find notes in progress to Paul, resting in the clutch of the typewriter. I knew that these letters were going either to Mr. Shaffer or to Mr. (Paul) Simon—men who bore the same initials as my father and who were also small and Jewish. It was a coincidence that fascinated me and caused me to believe they were all of the same pale pygmy tribe of funnymen—one I'd hopefully marry into someday.

In 2009, with only a brief history of polite exchanges between us, I reached out to Paul. I was in bad shape. My dad, Phil Spector, had just been convicted of murder and shuttled off to prison. I got Paul's number from my mother, left him a voice message, and heard back from him within 15 minutes. We had lunch the next day. Our friendship has since grown, as has his avuncular role in my life. He is unblinkingly benevolent. When I got laid off from my job in publishing and was broke, he paid for my dog's emergency surgery. He wrote a funny blurb for my first book, the satirical mash-up, Fifty Shades of Dorian Gray (2012). No matter how unconvinced I am of any success in my career, Paul, like a good uncle, is always impressed.

Rather than going out to eat as we normally would, we recently met in his office on the 11th floor of 1697 Broadway, the Ed Sullivan Theater, which, for the past 22 years has been home to Late Show with David Letterman. To say his office is large, doesn't do it justice—Paul's space is roughly twice the size of the bedroom I share in Bushwick with my fiancé. The walls are decorated with framed vintage posters. A Baldwin piano stands staunchly in an oblong corner.

"I think it was Carole King on Tapestry who said where you lead I will follow," Paul said, as I turned on the recorder. And so I led him into "the Dark Ages," as he calls it, when he was a part of Saturday Night Live, from 1975 to 1980.

Julia Roberts with Paul Shaffer and David Letterman on 'Late Show with David Letterman' in 2001

Paul started out on the show as a pianist, and then became a writer of special musical material, a position that, before he claimed it, "didn't even exist." That rare combination of musical acumen and comedic talent must have appealed to Lorne Michaels, too, as eventually Paul was performing on the show, both as a musician and as an actor. It was while working on SNL that he caught the eye and ear of David Letterman, who was planning another project now that his morning comedy show on NBC, The David Letterman Show, had been cancelled.

"[Dave] mentioned specifically the sketches that Bill Murray used to do [on SNL] when he was the sleazy lounge singer and I was playing the piano for him," said Paul. "Dave asked for me to come in for a meeting and claims that he never had anyone else in mind. I believe it. Other people on the staff had other ideas, but Dave's prevailed. We hit it off in this first meeting, and it was really quite as simple as that."

Bill Murray as a lounge singer in 'Saturday Night Live'

Letterman idolized Johnny Carson and set out to make a show in the mold of The Tonight Show Starring Johnny Carson, Paul says. Of course, Letterman wound up creating a mold of his own, with one of the most immediate distinctions being the fact that its bandleader and sidekick existed as one person: Paul Shaffer.

"Johnny Carson had his sidekick Ed, and his bandleader Doc, and I used to say, 'I'm a combination of Doc and Ed. You put them together, you get Dead,'" Paul said. "I put the two jobs together and now that's become a standard."

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Paul came to New York right around the same time fellow Canadians Eugene Levy and Martin Short made their way over in the early 70s. The three were best friends then and still are today. It's quite possible that had Letterman not come along with his offer, Paul would have pursued comedic work similar to that which "Marty," as he calls him, and Eugene pursued. But then there's that whole music thing. For Paul, saying yes to an opportunity to combine both comedy and music on a well-paying network TV gig was a no-brainer.

Plus, there was creative freedom—more so than one may expect—not just during the Letterman show, outside of which he had roles in 1984's This Is Spinal Tap among other feature films, but also on the show.

"Dave has expressed to me on so many occasions, 'If you have something of comedic value, jump in. I don't care if it's during my monologue, or an interview with a guest, just go for it,'" Paul told me. "What amazing freedom it is. You don't find that anywhere else."

The improvisational nature of the show has intimidated some celebrity guests, Paul admits. There are no rehearsals whatsoever—not after so many failed attempts in the early days.

"Dave used to come to the studio and we would try to rehearse bits, but we weren't good at rehearsing and it was just frustrating, especially to Dave. So he stopped coming to the rehearsals and that's when it really got a lot more fun."

And what fun they've had—especially in the early years over at NBC, when Late Night aired at 12:30 AM.

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"I don't know if the stakes were not as high but whatever it was, going on that late gave us the license to go way nuttier than we ever would have at 11:30," Paul said. "Once we came over here and changed to 11:30, things got a little bit more, I don't know, high-powered, and less chances were taken. Recently, we did a show that was really fun, mainly just for us, that we taped at 4:30 AM, just for the hell of it, really."

While Paul will often, without a hint of irony, refer to Letterman as "my boss," when talking about Dave, he'll also allude to the close friendship they've built. Back when they were both single guys, they'd double-date together. Nowadays, during summer, they hang out on Dave's ranch in Montana, and it's more of a family affair. Paul brings his wife, Cathy, and his two kids, Victoria and Will, and everyone goes horseback riding.

Always, Paul will mention how lucky and thankful he is, for this loyal friendship with Dave and this career that has been "an honor and a privilege and a gas." He doesn't hint at any loose ends that need tying, or any regret that the show is retiring. He's less placid when faced with the prospect of his own retirement, however.

"I'm not really a suburban guy," Paul explained, referring to his home in Westchester. "Maybe that in itself is going to keep me working—finding excuses to come into Manhattan. I'll have to figure something out."

Then again, Paul has a sense that in show business, it's not all up to you. "Eugene [Levy] summed it up for me," he said. "He said, 'Listen Paul, if the phone doesn't ring, you're retired.'"

The finale of The Late Show with David Letterman airs tonight at 11:35 PM on CBS.

Nicole Audrey Spector is a weekly contributor to the New Yorker's Goings On About Town section. Her work has appeared in the Atlantic, Salon, and elsewhere. She is also the author of Fifty Shades of Dorian Gray. Follow her on Twitter.